Diethyl Ether → 875307-00-9

HRID 855330Notes

Reaction equation

HRID 855330 reaction equation
[CH3:1][Mg]Br.COC(=O)[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[Cl:14].[Cl-].[NH4+].CC[O:20][CH2:21][CH3:22]>C1COCC1>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C:21]([OH:20])([CH3:22])[CH3:1])=[C:8]([Cl:14])[CH:9]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 22058730Methyl 4-Bromo-2-chlorobenzoateHCID 178418573HCID 178418573, compound

Product 1

HCID 58764285875307-00-9

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.88 ml of a 3 molar solution of methyl magnesium bromide in ether were added dropwise to a solution of 470 mg (1.88 mmol) of 4-bromo-2-chloro-benzoic acid methyl ester [CAS 185312-82-7] in 20 ml THF at −78° C. The reaction mixture was then warmed to rt and stirred overnight. The mixture was then poured into sat. ammonium chloride solution and extracted with ether. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography (0 to 20% ether in pentane). The title compound was obtained as a colorless liquid (415 mg, 82%). 1H NMR (CDCl3, 300 MHz): δ 1.71 (s, 6H), 2.39 (s, 1H), 7.38 (dd, J=8.5 and 2.1 Hz, 1H), 7.52 (d, J=2.1 Hz, 1H), 7.58 (d, J=8.5 Hz, 1H).

Workup

  1. extractionextracted with ether
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a residue which
  7. customwas purified by flash column chromatography (0 to 20% ether in pentane)

Sources & evidence

ORD record
ord-24916f2f52e34ebf9eab85fa15ac451d
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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